Polymers and copolymers of high glass transition temperature from hindered phenols

Abstract

Polymers and copolymers having high glass transition temperature and which are soluble in organic solvents are produced from highly hindered biphenols, in particular polyetherketones, polyethersulfones, polyesters and polyetherimides, as well as copolymers based on these polymers may be produced for a variety of applications.

We claim: 
     
       1. A homopolymer or copolymer containing units of formula: ##STR23## wherein R 1  and R 2  are the same and are selected from methyl, phenyl, naphthyl, p-fluorophenyl, p-chlorophenyl and p-bromophenyl, or one of R 1  and R 2  is hydrogen and the other is chlorine; y is fluorine;   m is 0, 1, 2, 3, 4 or 5; and   Z is a divalent linkage of formula: ##STR24## in which X is --CO-- or --SO 2  --; or ##STR25## in which R 3  is an aromatic hydrocarbon radical or aromatic hydrocarbon ether radical having from 6 to 20 carbon atoms, and halogenated derivatives thereof.   
     
     
       2. A homopolymer or copolymer of claim 1, in which R 1  and R 2  are methyl or phenyl and m is 0. 
     
     
       3. A homopolymer or copolymer containing units of formula: ##STR26## wherein R 1  and R 2  are methyl or phenyl. 
     
     
       4. A homopolymer or copolymer containing units of formula: ##STR27## wherein R 1  and R 2  are methyl or phenyl. 
     
     
       5. A process for producing a homopolymer or copolymer of formula (V): ##STR28## wherein R 1  and R 2  are the same and are selected from methyl, phenyl, naphthyl, p-fluorophenyl, p-chlorophenyl and p-bromophenyl, or one of R 1  and R 2  is hydrogen and the other is chlorine; X is a radical --CO-- or --SO 2  --;   Y is fluorine;   m is 0, 1, 2, 3, 4 or 5;   x is an integer of at least 1;   y is 0 or an integer of 1 or more;   x+y=n, and n is an integer of 2 to 200; and   C p  is derived from a comonomer, comprising reacting a biphenol of formula (III): ##STR29##  in which R 1 , R 2 , Y and m are as defined above, and a comonomer, if desired, with a compound of formula (VI): ##STR30## in which Hal is fluorine or chlorine and X is as defined above.   
     
     
       6. A process according to claim 5, in which said reacting is carried out in the presence of a base in a polar aprotic solvent. 
     
     
       7. A process according to claim 6, in which said base is potassium carbonate. 
     
     
       8. A process according to claim 6, in which R 1  and R 2  are methyl or phenyl, m is 0, X is --CO-- and y is 0. 
     
     
       9. A process according to claim 6, in which R 1  and R 2  are methyl or phenyl, m is 0, X is --SO 2  -- and y is 0. 
     
     
       10. A process according to claim 7, carried out under reflux.